By 2016 an estimated 95% of all commercial software packages will include Open Source Software (OSS). This extended adoption is yet not avoiding failure rates in OSS projects to be as high as 50%. Inadequate risk management has been identified among the top mistakes to avoid when implementing OSS-based solutions. Understanding, managing and mitigating OSS adoption risks is therefore crucial to avoid potentially significant adverse impact on the business. In this position paper we portray a short report of work in progress on risk management in OSS adoption processes. We present a risk-aware technical decision-making management platform integrated in a business-oriented decision-making framework, which together support placing technical OSS adoption decisions into organizational, business strategy as well as the broader OSS community context. The platform will be validated against a collection of use cases coming from different types of organizations: big companies, SMEs, public administration, consolidated OSS communities and emergent small OSS products.